Showing Compound Card for Isovaleraldehyde (CDB000686)

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Record Information
Version1.0
Created at2020-03-19 00:51:08 UTC
Updated at2020-12-07 19:07:40 UTC
CannabisDB IDCDB000686
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsovaleraldehyde
DescriptionIsovaleraldehyde, also known as 3-methyl-butanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. It exists as a clear colorless or slightly yellow liquid and can be found in essentially all eukaryotes, from yeast to plants to humans. It can be naturally produced through the colonic or microbial breakdown of the amino acid leucine. It can also be generated through the breakdown of leucine in malt (for beer) via reductones. Isovaleraldehyde has been found in elevated concentrations in plasma certain cases of hepatic encephalopathy, however not significantly (PMID: 4038637 ). Bacteroides (microbial) fermentation of carbohydrates in the gut produces ethanoic, propionic, butanoic, pentanoic, and hexanoic acids leading to the production of aldehydes, such as iosvaleraldehyde (PMID: 17314143 , 18275147 , 18175918 , 16899660 ). Isovaleraldehyde is found in low amounts in many types of foods including beer, spirits (rum, sake, wine), cheese, coffee, chicken, fish, chocolate, corn tortillas, olive oil and tea. Isovaleraldehyde has also been detected, but not quantified in, several different fruits and nuts, such as muskmelons, highbush blueberries, fenugreeks, hazelnuts, and dills. Isovaleraldehyde has an ethereal, aldehydic chocolate, peach or fatty odor. It exhibits a fruity, nutty, chocolate or cocoa-like taste. As a result, isovaleraldehyde is used as a food additive and as a perfuming or masking agent. Isovaleraldehyde can be produced commercially and is used as a reagent for the production of pharmaceuticals and pesticides. Notably it is used to synthesize pinacolone, which is a precursor for a number of pesticides. Isovaleraldehyde has also been reported to be found in Cannabis sativa (PMID: 6991645 , 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-MethylbutyraldehydeChEBI
beta-MethylbutanalChEBI
Iso-C4H9CHOChEBI
Isoamyl aldehydeChEBI
IsopentaldehydeChEBI
IsovaleralChEBI
IsovalerylaldehydeChEBI
b-MethylbutanalGenerator
Β-methylbutanalGenerator
IsovaleraldehydeChEBI
2-Methylbutanal-4HMDB
3-Methyl-1-butanalHMDB
3-Methyl-butanalHMDB
3-Methyl-butyraldehydeHMDB
3-Methylbutan-1-alHMDB
3-MethylbutanalHMDB
IsoamylaldehydeHMDB
IsopentanalHMDB
Isovaleric aldehydeHMDB
Methyl butanalHMDB
iso-ValeraldehydeHMDB
Chemical FormulaC5H10O
Average Molecular Weight86.13
Monoisotopic Molecular Weight86.0732
IUPAC Name3-methylbutanal
Traditional Nameisovaleraldehyde
CAS Registry Number590-86-3
SMILES
CC(C)CC=O
InChI Identifier
InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
InChI KeyYGHRJJRRZDOVPD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-51 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility14 mg/mL at 20 °CNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.29ALOGPS
logP1.05ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)18.56ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.49 m³·mol⁻¹ChemAxon
Polarizability10.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-881fcc89b0f579b407932015-03-01View Spectrum
GC-MSIsovaleraldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-3a38c8f6150bf1f43e74Spectrum
GC-MSIsovaleraldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5a3fd4f38dc36ebe58a1Spectrum
GC-MSIsovaleraldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-3a38c8f6150bf1f43e74Spectrum
GC-MSIsovaleraldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5a3fd4f38dc36ebe58a1Spectrum
Predicted GC-MSIsovaleraldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-4b322dc8237378d93057Spectrum
Predicted GC-MSIsovaleraldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-7f4ac528265c8b3bf3ab2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-6e4f25dc68765a0e52ca2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-809684cd2152204e911f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-3a38c8f6150bf1f43e742012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-5a3fd4f38dc36ebe58a12012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a8ed71d6e7d567b598b42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kp-9000000000-043451832d2f37b1c7e12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3c57d920ca714b174bb32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-030536579800c9e499402015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-be1f1229d7e13994d1502015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-13768c049fd8e5c234642015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a8ed71d6e7d567b598b42015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kp-9000000000-043451832d2f37b1c7e12015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3c57d920ca714b174bb32015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-030536579800c9e499402015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-be1f1229d7e13994d1502015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-13768c049fd8e5c234642015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2091e44a102d8284a8132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-199420ebca1b5eda63692021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-0f801351f709d0e5abf62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-fead34b12404197f107d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-cf72963a4f1f9f7f2df02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-cd0a0aa8e74bbc2b63442021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006478
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003285
KNApSAcK IDC00048949
Chemspider ID11065
KEGG Compound IDC07329
BioCyc IDCPD-7031
BiGG IDNot Available
Wikipedia LinkIsovaleraldehyde
METLIN IDNot Available
PubChem Compound11552
PDB IDNot Available
ChEBI ID16638
References
General References
  1. Marshall AW, DeSouza M, Morgan MY: Plasma 3-methylbutanal in man and its relationship to hepatic encephalopathy. Clin Physiol. 1985 Feb;5(1):53-62. doi: 10.1111/j.1475-097x.1985.tb00746.x. [PubMed:4038637 ]
  2. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. doi: 10.1096/fj.06-6927com. Epub 2007 Feb 21. [PubMed:17314143 ]
  3. Sampaio OM, Reche RV, Franco DW: Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification. J Agric Food Chem. 2008 Mar 12;56(5):1661-8. doi: 10.1021/jf0726841. Epub 2008 Feb 15. [PubMed:18275147 ]
  4. Tanimoto S, Matsumoto H, Fujii K, Ohdoi R, Sakamoto K, Yamane Y, Miyake M, Shimoda M, Osajima Y: Enzyme inactivation and quality preservation of sake by high-pressure carbonation at a moderate temperature. Biosci Biotechnol Biochem. 2008 Jan;72(1):22-8. doi: 10.1271/bbb.70297. Epub 2008 Jan 7. [PubMed:18175918 ]
  5. Whetstine ME, Drake MA, Broadbent JR, McMahon D: Enhanced nutty flavor formation in cheddar cheese made with a malty Lactococcus lactis adjunct culture. J Dairy Sci. 2006 Sep;89(9):3277-84. doi: 10.3168/jds.S0022-0302(06)72364-5. [PubMed:16899660 ]
  6. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  7. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]